Kissimmee vacation rentals

We found 32,084 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Kissimmee by choosing from 15175 houses, 1813 apartments, and other vacation rentals. Vacation homes provide the best amenities for you and your friends, family, or even pets, like WiFi and parking. At the end of the day, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Kissimmee

Showing deals for:Nov 14 - Nov 21

Image gallery for 14 Bedroom mansion that sleeps 40 people. Host your wedding reception here

Private pool
9.8 out of 10 rating
Exceptional
(27 reviews)

14 Bedroom mansion that sleeps 40 people. Host your wedding reception here

Kissimmee, FL

10% off
Price is CA $1,114
CA $10,686 total
includes taxes & fees
14 Bedroom mansion that sleeps 40 people. Host your wedding reception here

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Find out more about Kissimmee

Find out more about Kissimmee

Why visit Kissimmee

  1. Proximity to Disney Parks: Kissimmee is just minutes away from the magical Disney attractions, making it a prime location for family fun.
  2. Diverse Outdoor Activities: Enjoy a range of outdoor adventures, including lakeside relaxation, hiking, and family-friendly excursions.
  3. Welcoming Neighbourhoods: Experience friendly communities with a charming atmosphere, perfect for a peaceful retreat.
  4. Variety of Accommodations: Choose from private vacation homes, spacious villas, or cozy condos tailored to your needs.
  5. Cultural Experiences: Explore local arts centres and events that offer a taste of Kissimmee's vibrant culture.

Popular types of accommodation in Kissimmee

If you're exploring vacation rentals in Kissimmee, you're in for a treat! The most popular types of accommodations include houses, spacious villas, and cozy condos. Whether you're seeking the comforts of a home away from home or the convenience of a condo, Kissimmee offers a variety of options to suit your needs. Discover the best vacation rentals that provide transparency, savings, and reassurance for your perfect getaway!

  • Houses: The top choice for visitors to Kissimmee, these homes offer ample space and privacy, ideal for families or groups.
  • Villas: These spacious and luxurious accommodations are perfect for those seeking a relaxing getaway with modern amenities.
  • Condos: A popular option, condos provide a blend of comfort and convenience, often located near attractions.
  • Apartments: A practical choice for budget-conscious travellers, offering essential amenities for a pleasant stay.
  • Cottages: Quaint and charming, these cozy retreats are perfect for a peaceful escape in nature.**

Top attractions in Kissimmee

Kissimmee, Florida, is the perfect destination for family vacations, offering a blend of entertainment and cultural experiences. Visitors can explore popular attractions like theme parks, lakes, and arts centres while enjoying outdoor activities. Whether you're seeking family-friendly fun or a taste of local culture, Kissimmee has something for everyone. Don't forget to consider beachfront rentals for a relaxing stay by the water during your trip.

  1. Universal Orlando Resort: Experience thrilling rides and attractions based on beloved movies, with family-friendly entertainment and immersive experiences that will delight visitors of all ages.
  2. Orange County Convention Center: A hub of culture, this arts centre hosts a variety of events and exhibitions, showcasing local talent and international artistry in a vibrant atmosphere.
  3. Kissimmee Lakefront Park: Enjoy beautiful waterfront views, recreational activities, and picnic areas in this urban park, perfect for families seeking outdoor fun in a city setting.

Things to do recommended for couples

For a memorable couple's getaway in Kissimmee, enjoy a round of mini-golf at Congo River Golf, indulge in a romantic dinner at Pirate's Dinner Adventure, and unwind with a tasting at True Blue Winery. Each venue offers a unique blend of fun and intimacy for your vacation.

Things to do recommended for families

Families visiting Kissimmee can splash around at Aquatica, a fantastic waterpark nearby, enjoy sports at Austin-Tindall Regional Park, or unwind in the natural beauty of Shingle Creek Regional Park, offering a perfect blend of adventure, sports, and relaxation for everyone.

Things to do recommended for groups

Explore Disney Springs™ for a delightful shopping experience just 14.5km from Kissimmee. Visit Old Town for family-friendly entertainment and venture to Mystic Dunes Golf Club for a round of golf in the beautiful outdoor setting. Enjoy the vibrant vibes of this charming area!

What do I need to keep in mind when booking a vacation in Kissimmee

If you're planning a trip with a group, family, or pets, or if you're considering an extended stay, it's important to prioritize your preferences in your search. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Kissimmee with a group: Think about how many bedrooms you require, as well as features like a full kitchen or outdoor area for group gatherings. Fortunately, you can easily filter for all these options and more on Vrbo.
  • Traveling to Kissimmee with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, being close to family-friendly attractions is a wise consideration.
  • Taking your pets with you to Kissimmee: For many families, a vacation isn't truly special without their furry companion by their side. If you can relate to this, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home during your stay.
  • Planning for a long term stay visiting Kissimmee: If you’re searching for vacation rentals with discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider adding amenities such as a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay in Kissimmee

Kissimmee, Florida, is an ideal destination for family-friendly vacations, offering a sunny atmosphere and endless entertainment options. Just minutes away from the magical Disney parks, visitors can enjoy a variety of excursions and relax in welcoming neighborhoods. Whether you're seeking thrilling adventures or a peaceful retreat, the Kissimmee area promises a memorable experience filled with friendly people and delightful activities for all ages.

  • Four Corners: Four Corners is a charming village located near Kissimmee, known for its family-friendly atmosphere and outdoor adventures. Visitors flock here for a variety of entertainment options, including resort amenities and scenic golf courses. Nearby attractions like theme parks, film studios, and a stadium provide plenty of excitement for all ages. The area combines a relaxed vibe with easy access to thrilling adventures, making it an ideal spot for families looking to create lasting memories.
  • Windsor Hills: Nestled around Kissimmee, Windsor Hills is a vibrant neighborhood that caters to families and outdoor enthusiasts. The area boasts a mix of resorts and shopping areas, ensuring visitors have everything they need at their fingertips. With proximity to renowned theme parks, film studios, and a stadium, Windsor Hills is a fantastic base for exploring the many attractions of Central Florida. This welcoming community offers a perfect blend of leisure and excitement, appealing to tourists of all ages.
  • Reunion: Reunion is a picturesque neighborhood located near Kissimmee, perfect for those seeking outdoor activities and sports experiences. The area offers an array of resorts and golf courses that cater to both relaxation and adventure. With its close proximity to theme parks, film studios, and even nearby beaches, Reunion provides a diverse range of attractions for visitors. Whether you're hitting the links or soaking up the sun, this neighborhood is a delightful destination for families and active travellers alike.

Booking with Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to refine your search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage your travel arrangements with ease. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

The sunny setting of Kissimmee is ready to explore

Take a vacation to Kissimmee and enjoy the area's festivals, entertainment and opera. Renowned for its theme park, shopping and sporting events, this city welcomes all visitors. Disney's Animal Kingdom® Theme Park and Walt Disney World® Resort are just a couple of the must-sees. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Kissimmee

Do you want to discover attractions to see while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Kissimmee a fun place to get away. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Epcot® (10.2 mi / 16.4 km)
  • Disney's Animal Kingdom® Theme Park (12.1 mi / 19.5 km)
  • Universal Orlando Resort (13 mi / 21 km)
  • Universal Studios Florida (13.4 mi / 21.6 km)
  • Walt Disney World® Resort (13.6 mi / 21.9 km)
  • Magic Kingdom® Park (13.7 mi / 22 km)

Exploring the natural landscape of Kissimmee

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Kissimmee is a great place to get out in nature. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Kissimmee Lakefront Park (0.2 mi / 0.3 km)
  • Osceola Heritage Park (2.4 mi / 3.9 km)
  • Lake Tohopekaliga (6.1 mi / 9.9 km)
  • Lake Bryan (7.5 mi / 12.1 km)
  • Austin-Tindall Regional Park (8.3 mi / 13.4 km)
  • Lake Butler (14.4 mi / 23.2 km)

Seasonal weather in Kissimmee

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 81°F.

How to get to and around Kissimmee

The nearest airport is in Kissimmee, FL (ISM-Kissimmee Gateway), located 1.8 mi (2.9 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Orlando Intl. Airport (MCO), which is 11.4 mi (18.3 km) away.

If you're traveling by train, the main station is Kissimmee Station. Consider catching the metro at Tupperware Station or Poinciana Station to see more of the city.

Frequently asked questions

What is the best area to stay in Kissimmee when booking a vacation rental?
When considering a vacation rental in Kissimmee, Florida, a popular area to stay is the bustling neighbourhood of Celebration. This charming community, originally developed by The Walt Disney Company, boasts picturesque streets lined with vibrant shops and delightful dining options. It's a fantastic spot for families, and you'll find a variety of properties available, ranging from cosy apartments to spacious villas, making it a flexible choice for different group sizes.

Just a stone's throw away from Celebration is the iconic Walt Disney World Resort, which is a top attraction for visitors of all ages. The enchanting theme parks and entertainment options offer countless opportunities for fun and adventure. Additionally, the nearby Old Town in Kissimmee provides a unique blend of shopping, dining, and entertainment, including classic car shows and amusement rides, making it a great spot for an evening stroll.

Another excellent area to consider is the Formosa Gardens neighbourhood, which features a wealth of vacation rentals that cater to larger groups and families. This area is particularly close to the attractions of both Disney and Universal Studios, ensuring that guests can easily access some of Florida's most famous entertainment. The proximity to the bustling Highway 192 means guests can also enjoy a variety of restaurants, shops, and other amenities without straying too far from home.
How much does it cost to rent a vacation home in Kissimmee?
Prices for vacation rentals in Kissimmee vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Kissimmee to more spacious homes.
Are there any discounts for Kissimmee vacation house rentals?
You can find great discounts on house rentals in Kissimmee on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Kissimmee?
For renting a beach house in Kissimmee, Florida, travellers should consider the nearby areas along the shores of Lake Tohopekaliga, which is known for its beautiful waterfront views and recreational activities. The area around Kissimmee Lakefront Park offers a range of vacation rentals, including charming lakefront cottages and spacious family homes. Many of these properties come with amenities such as private docks, outdoor grills, and screened porches, ideal for enjoying the warm Florida weather and picturesque sunsets over the water.

Additionally, the nearby community of Celebration provides a quaint atmosphere with its tree-lined streets and beautiful parks. Here, visitors can find well-appointed homes that often feature modern kitchens, community pools, and access to walking trails. The proximity to local shops and dining options further enhances the appeal of this area.

For those looking for a more vibrant atmosphere, the resorts near the Kissimmee area offer luxurious options with resort-style amenities, such as swimming pools, fitness centres, and on-site dining. This makes it easy for families to have fun-filled days without straying too far from their accommodation. Find your rental near the beach in Kissimmee.
Are there any houseboat rentals in Kissimmee?
In Kissimmee, houseboat rentals are indeed available, providing a unique way to experience the waterways of Florida. These rentals are typically located in scenic areas near Lake Tohopekaliga, offering stunning views and a tranquil atmosphere. Travellers can expect amenities such as comfortable sleeping quarters, kitchen facilities for preparing meals, and outdoor decks for enjoying the sunshine and fresh air. Some houseboats may also feature additional luxuries like hot tubs or water sports equipment, suiting those looking for adventure on the water.
What is the most popular type of vacation rental accomodation in Kissimmee?
In Kissimmee, vacation houses are the most popular type of rental, with approximately 12,288 available throughout the area. These properties are often spacious and well-suited for families or larger groups, featuring multiple bedrooms, fully equipped kitchens, private pools, and outdoor spaces superb for relaxation after a day at the nearby theme parks, such as Walt Disney World and Universal Studios.
Are there any family house rentals in Kissimmee?
In Kissimmee, there is a wealth of family-friendly house rentals available, with around 14,642 options to choose from. This vibrant area is known for its proximity to major attractions such as Walt Disney World Resort and Universal Orlando Resort, making it an ideal base for families seeking adventure.

Many properties in Kissimmee boast spacious living areas, fully equipped kitchens great for preparing meals after a day of exploring, and private outdoor spaces where children can play. Travellers can also expect amenities like Wi-Fi, air conditioning, and sometimes even private pools or game rooms, ensuring a comfortable and enjoyable stay for everyone. See all family-friendly rentals in Kissimmee.
Can I rent a vacation home with a pool or hot tub in Kissimmee?
In Kissimmee, there are an impressive number of vacation homes available for rent that feature pools and hot tubs, with around 17,774 options to choose from. This popular destination is well-known for its proximity to major theme parks, making it a favourite for families and groups. Many rentals can be found in neighbourhoods such as Windsor Hills and Emerald Island, both of which offer a range of community amenities alongside private accommodations. Find your rental in Kissimmee with a pool or a hot tub.
Can I find long-stay vacation rentals in Kissimmee?
A long-stay vacation rental in Kissimmee is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Kissimmee?
In Kissimmee, there are numerous pet-friendly house rentals available, with over 3,000 options to choose from. Many of these vacation homes come equipped with amenities like private pools, spacious backyards, and fully furnished kitchens, providing a comfortable and homely environment for both travellers and their pets. See all pet-friendly rentals in Kissimmee.
Are there any remote work vacation rentals in Kissimmee?
In Kissimmee, Florida, there is an impressive selection of remote work vacation rentals, with around 18,012 options available. This vibrant area, located near the renowned theme parks, offers various properties tailored for those looking to balance work and leisure. Many of these rentals come equipped with dedicated workspaces, high-speed Wi-Fi, and amenities such as desks, laptop-compatible safes, and comfortable office chairs, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Kissimmee vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Kissimmee with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Kissimmee?
In Kissimmee, popular rental amenities include a variety of options to enhance the vacation experience. Many properties feature fully equipped kitchens, which allow guests to prepare their own meals, adding convenience and flexibility during their stay. A significant number of rentals also offer access to pools, with both shared and private options available, including heated pools for year-round enjoyment.
When is the best time to visit Kissimmee for a vacation rental?
The peak season for visiting Kissimmee is during the summer months, from June to August, with July being the most popular time for vacation rentals. This vibrant period attracts families and adventure seekers eager to experience the excitement of nearby attractions such as Walt Disney World and Universal Studios, as well as the natural beauty of the surrounding area.

During these summer months, expect warm temperatures averaging around 32°C, making it superb for enjoying outdoor activities, from theme park adventures to exploring the scenic parks and lakes nearby. Kissimmee offers a lot of options for sightseeing, and the lively atmosphere adds to the overall enjoyment of your vacation.

For those looking to travel on a budget, October presents a fantastic opportunity to visit Kissimmee. The weather remains pleasant, with temperatures in the mid to high 20s Celsius, and the crowds begin to thin out, allowing for a more relaxed experience. This month is ideal for enjoying the local attractions and perhaps even taking part in Halloween festivities, which add a unique charm to the area.
How early should I book a Kissimmee vacation rental?
Book your Kissimmee vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Kissimmee?
In Kissimmee, visitors can discover a range of attractions that cater to various interests. The area is renowned for its proximity to the Walt Disney World Resort, where vacation rentals can be found in neighbourhoods such as Celebration, a charming community designed with a nostalgic feel, offering easy access to the parks.

Moreover, the Old Town district features a mix of shops, restaurants, and entertainment options, providing a lively atmosphere. Here, guests can enjoy classic car shows and amusement rides, making it a great spot for family outings.
Can I change or cancel my Kissimmee home rental booking on Vrbo?
To find Kissimmee vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Kissimmee vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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